US6458501B1 - Forming a toner using surfactant-free emulsion polymerization - Google Patents
Forming a toner using surfactant-free emulsion polymerization Download PDFInfo
- Publication number
- US6458501B1 US6458501B1 US09/409,690 US40969099A US6458501B1 US 6458501 B1 US6458501 B1 US 6458501B1 US 40969099 A US40969099 A US 40969099A US 6458501 B1 US6458501 B1 US 6458501B1
- Authority
- US
- United States
- Prior art keywords
- surfactant
- process according
- latex
- initiator
- polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000007720 emulsion polymerization reaction Methods 0.000 title claims description 21
- 239000004816 latex Substances 0.000 claims abstract description 102
- 229920000126 latex Polymers 0.000 claims abstract description 102
- 239000000178 monomer Substances 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 64
- 230000008569 process Effects 0.000 claims abstract description 62
- 229920000642 polymer Polymers 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 59
- 239000003999 initiator Substances 0.000 claims abstract description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000004094 surface-active agent Substances 0.000 claims abstract description 36
- 150000003254 radicals Chemical class 0.000 claims abstract description 21
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 239000002245 particle Substances 0.000 claims description 67
- 239000000049 pigment Substances 0.000 claims description 25
- 239000003086 colorant Substances 0.000 claims description 15
- 239000006185 dispersion Substances 0.000 claims description 13
- 239000012986 chain transfer agent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000004931 aggregating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 abstract description 56
- 238000004220 aggregation Methods 0.000 abstract description 16
- 230000002776 aggregation Effects 0.000 abstract description 16
- -1 2,2′-azobisisobutyl amide dihydrate Chemical class 0.000 description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 28
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 26
- 239000008367 deionised water Substances 0.000 description 25
- 229910021641 deionized water Inorganic materials 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 239000013049 sediment Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 13
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000004581 coalescence Methods 0.000 description 8
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 7
- 239000002002 slurry Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000010959 steel Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000004945 emulsification Methods 0.000 description 4
- 238000005189 flocculation Methods 0.000 description 4
- 230000016615 flocculation Effects 0.000 description 4
- 150000002222 fluorine compounds Chemical class 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- 238000004255 ion exchange chromatography Methods 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 238000001139 pH measurement Methods 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 3
- VKWNTWQXVLKCSG-UHFFFAOYSA-N n-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 3
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 3
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 3
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- ZHUWXKIPGGZNJW-UHFFFAOYSA-N 6-methylheptyl 3-sulfanylpropanoate Chemical compound CC(C)CCCCCOC(=O)CCS ZHUWXKIPGGZNJW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- WNWZKKBGFYKSGA-UHFFFAOYSA-N n-(4-chloro-2,5-dimethoxyphenyl)-2-[[2,5-dimethoxy-4-(phenylsulfamoyl)phenyl]diazenyl]-3-oxobutanamide Chemical compound C1=C(Cl)C(OC)=CC(NC(=O)C(N=NC=2C(=CC(=C(OC)C=2)S(=O)(=O)NC=2C=CC=CC=2)OC)C(C)=O)=C1OC WNWZKKBGFYKSGA-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WTXXSZUATXIAJO-OWBHPGMISA-N (Z)-14-methylpentadec-2-enoic acid Chemical compound CC(CCCCCCCCCC\C=C/C(=O)O)C WTXXSZUATXIAJO-OWBHPGMISA-N 0.000 description 1
- CDDDRVNOHLVEED-UHFFFAOYSA-N 1-cyclohexyl-3-[1-[[1-(cyclohexylcarbamoylamino)cyclohexyl]diazenyl]cyclohexyl]urea Chemical compound C1CCCCC1(N=NC1(CCCCC1)NC(=O)NC1CCCCC1)NC(=O)NC1CCCCC1 CDDDRVNOHLVEED-UHFFFAOYSA-N 0.000 description 1
- QAQSNXHKHKONNS-UHFFFAOYSA-N 1-ethyl-2-hydroxy-4-methyl-6-oxopyridine-3-carboxamide Chemical compound CCN1C(O)=C(C(N)=O)C(C)=CC1=O QAQSNXHKHKONNS-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- TXWSZJSDZKWQAU-UHFFFAOYSA-N 2,9-dimethyl-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(C)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)C)N1)C1=C2 TXWSZJSDZKWQAU-UHFFFAOYSA-N 0.000 description 1
- AVTLBBWTUPQRAY-UHFFFAOYSA-N 2-(2-cyanobutan-2-yldiazenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)N=NC(C)(CC)C#N AVTLBBWTUPQRAY-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- XCKGFJPFEHHHQA-UHFFFAOYSA-N 5-methyl-2-phenyl-4-phenyldiazenyl-4h-pyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC=C1 XCKGFJPFEHHHQA-UHFFFAOYSA-N 0.000 description 1
- ZFSPZXXKYPTSTJ-UHFFFAOYSA-N 5-methyl-2-propan-2-yl-4,5-dihydro-1h-imidazole Chemical compound CC(C)C1=NCC(C)N1 ZFSPZXXKYPTSTJ-UHFFFAOYSA-N 0.000 description 1
- ZSBNXOIAJFVXMP-UHFFFAOYSA-N 5-tert-butyl-2-methylbenzenethiol Chemical compound CC1=CC=C(C(C)(C)C)C=C1S ZSBNXOIAJFVXMP-UHFFFAOYSA-N 0.000 description 1
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
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- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000006177 alkyl benzyl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
- 229940077484 ammonium bromide Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000001000 anthraquinone dye Chemical class 0.000 description 1
- YYGRIGYJXSQDQB-UHFFFAOYSA-N anthrathrene Natural products C1=CC=CC2=CC=C3C4=CC5=CC=CC=C5C=C4C=CC3=C21 YYGRIGYJXSQDQB-UHFFFAOYSA-N 0.000 description 1
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- WMLFGKCFDKMAKB-UHFFFAOYSA-M benzyl-diethyl-tetradecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](CC)(CC)CC1=CC=CC=C1 WMLFGKCFDKMAKB-UHFFFAOYSA-M 0.000 description 1
- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
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- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- FPDLLPXYRWELCU-UHFFFAOYSA-M dimethyl(dioctadecyl)azanium;methyl sulfate Chemical compound COS([O-])(=O)=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC FPDLLPXYRWELCU-UHFFFAOYSA-M 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
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- 230000004927 fusion Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- MTZWHHIREPJPTG-UHFFFAOYSA-N phorone Chemical compound CC(C)=CC(=O)C=C(C)C MTZWHHIREPJPTG-UHFFFAOYSA-N 0.000 description 1
- 229940110337 pigment blue 1 Drugs 0.000 description 1
- 229940099800 pigment red 48 Drugs 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical class Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G9/00—Developers
- G03G9/08—Developers with toner particles
- G03G9/0802—Preparation methods
- G03G9/0804—Preparation methods whereby the components are brought together in a liquid dispersing medium
- G03G9/0806—Preparation methods whereby the components are brought together in a liquid dispersing medium whereby chemical synthesis of at least one of the toner components takes place
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/115—Cationic or anionic
Abstract
Description
Claims (18)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/409,690 US6458501B1 (en) | 1999-09-30 | 1999-09-30 | Forming a toner using surfactant-free emulsion polymerization |
JP2000292111A JP2001131214A (en) | 1999-09-30 | 2000-09-26 | Method for manufacturing latex polymer |
EP00121137A EP1088833B1 (en) | 1999-09-30 | 2000-09-28 | Surfactant-free emulsion polymerization process |
DE60010192T DE60010192T2 (en) | 1999-09-30 | 2000-09-28 | Surfactant-free emulsion polymerization process |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/409,690 US6458501B1 (en) | 1999-09-30 | 1999-09-30 | Forming a toner using surfactant-free emulsion polymerization |
Publications (2)
Publication Number | Publication Date |
---|---|
US20020049275A1 US20020049275A1 (en) | 2002-04-25 |
US6458501B1 true US6458501B1 (en) | 2002-10-01 |
Family
ID=23621583
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/409,690 Expired - Lifetime US6458501B1 (en) | 1999-09-30 | 1999-09-30 | Forming a toner using surfactant-free emulsion polymerization |
Country Status (4)
Country | Link |
---|---|
US (1) | US6458501B1 (en) |
EP (1) | EP1088833B1 (en) |
JP (1) | JP2001131214A (en) |
DE (1) | DE60010192T2 (en) |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050163925A1 (en) * | 2004-01-28 | 2005-07-28 | Xerox Corporation | Emulsion aggregation process for forming curable powder coating compositions, curable powder coating compositions and method for using the same |
US20050165133A1 (en) * | 2004-01-28 | 2005-07-28 | Xerox Corporation | Emulsion aggregation process for forming powder coating compositions, powder coating compositions and method for using the same |
US20060154167A1 (en) * | 2005-01-13 | 2006-07-13 | Xerox Corporation | Emulsion aggregation toner compositions |
US20070043156A1 (en) * | 2003-05-06 | 2007-02-22 | Nuplex Resines B.V. | Emulsion polymerization process, polymer dispersion and film-forming composition |
US20070059630A1 (en) * | 2005-09-09 | 2007-03-15 | Xerox Corporation | Emulsion polymerization process |
US20080299479A1 (en) * | 2007-05-31 | 2008-12-04 | Xerox Corporation | Toner compositions |
US20080299478A1 (en) * | 2007-05-31 | 2008-12-04 | Xerox Corporation | Toner compositions |
US20090061342A1 (en) * | 2007-09-05 | 2009-03-05 | Xerox Corporation | Toner compositions |
US20090081576A1 (en) * | 2007-09-25 | 2009-03-26 | Xerox Corporation | Toner compositions |
US20090263740A1 (en) * | 2008-04-21 | 2009-10-22 | Xerox Corporation | Toner compositions |
EP2172812A1 (en) | 2008-10-06 | 2010-04-07 | Xerox Corporation | Toner containing fluorescent nanoparticles |
US20100086701A1 (en) * | 2008-10-06 | 2010-04-08 | Xerox Corporation | Radiation curable ink containing fluorescent nanoparticles |
US8147714B2 (en) | 2008-10-06 | 2012-04-03 | Xerox Corporation | Fluorescent organic nanoparticles and a process for producing fluorescent organic nanoparticles |
US8236198B2 (en) | 2008-10-06 | 2012-08-07 | Xerox Corporation | Fluorescent nanoscale particles |
US8586141B2 (en) | 2008-10-06 | 2013-11-19 | Xerox Corporation | Fluorescent solid ink made with fluorescent nanoparticles |
EP3133115A1 (en) | 2015-08-14 | 2017-02-22 | King Abdulaziz City for Science and Technology | Polymer-encapsulated carbon black: process for its preparation and use thereof |
US10294355B2 (en) | 2014-10-13 | 2019-05-21 | Avery Dennison Corporation | Vinyl acetate-ethylene/acrylic polymer emulsions and products and methods relating thereto |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1854433B1 (en) * | 1999-10-22 | 2010-05-12 | FSI Acquisition Sub, LLC | Facet arthroplasty devices |
US7223508B2 (en) | 2004-03-22 | 2007-05-29 | Konica Minolta Holdings, Inc. | Toner for developing electrostatic image, method for producing the toner and image forming method |
EP2240518A2 (en) * | 2008-02-11 | 2010-10-20 | Merck Patent GmbH | Fluid compositions for colour electrophoretic displays |
US10093752B2 (en) * | 2013-06-13 | 2018-10-09 | Gwangju Institute Of Science And Technology | Homopolymer nanoparticles by self-emulsion polymerization reaction and preparation method thereof |
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JPS6011926B2 (en) * | 1977-05-09 | 1985-03-29 | 株式会社クラレ | Method for producing transparent impact-resistant methyl methacrylate resin |
JPS61241310A (en) * | 1985-04-18 | 1986-10-27 | Soken Kagaku Kk | Production of emulsion of crosslinked polymer |
-
1999
- 1999-09-30 US US09/409,690 patent/US6458501B1/en not_active Expired - Lifetime
-
2000
- 2000-09-26 JP JP2000292111A patent/JP2001131214A/en active Pending
- 2000-09-28 DE DE60010192T patent/DE60010192T2/en not_active Expired - Lifetime
- 2000-09-28 EP EP00121137A patent/EP1088833B1/en not_active Expired - Lifetime
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US3882070A (en) * | 1973-05-23 | 1975-05-06 | Arco Polymers Inc | Persulfate stabilized latices |
EP0022633B1 (en) | 1979-06-26 | 1985-02-20 | Rohm And Haas Company | Process for making multistage polymer particles, product thus obtained, process for making aqueous dispersions of these particles, product thus obtained, process for making films, compositions for coating and/or impregnating, multistage polymers and their use |
US4427836A (en) * | 1980-06-12 | 1984-01-24 | Rohm And Haas Company | Sequential heteropolymer dispersion and a particulate material obtainable therefrom, useful in coating compositions as a thickening and/or opacifying agent |
US4378272A (en) * | 1981-06-24 | 1983-03-29 | Gaf Corporation | Water purifying latex binder |
US5346797A (en) | 1993-02-25 | 1994-09-13 | Xerox Corporation | Toner processes |
US5418108A (en) | 1993-06-25 | 1995-05-23 | Xerox Corporation | Toner emulsion aggregation process |
US5455315A (en) * | 1994-06-06 | 1995-10-03 | Xerox Corporation | Emulsion polymerization processes and toners thereof |
WO1998039372A1 (en) * | 1997-03-05 | 1998-09-11 | Neste Chemicals Oy | A method for the preparation of hollow polymer particle latex |
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Cited By (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070043156A1 (en) * | 2003-05-06 | 2007-02-22 | Nuplex Resines B.V. | Emulsion polymerization process, polymer dispersion and film-forming composition |
US20110152452A1 (en) * | 2003-05-06 | 2011-06-23 | Nuplex Resins Bv | Emulsion polymerization process, polymer dispersion and film-forming composition |
US20050163925A1 (en) * | 2004-01-28 | 2005-07-28 | Xerox Corporation | Emulsion aggregation process for forming curable powder coating compositions, curable powder coating compositions and method for using the same |
US7501150B2 (en) | 2004-01-28 | 2009-03-10 | Xerox Corporation | Emulsion aggregation process for forming powder coating compositions, powder coating compositions and method for using the same |
EP1559751A2 (en) | 2004-01-28 | 2005-08-03 | Xerox Corporation | Emulsion aggregation process for forming curable powder coating compositions, curable powder coating compositions and method for using the same |
US7985524B2 (en) | 2004-01-28 | 2011-07-26 | Xerox Corporation | Emulsion aggregation process for forming curable powder coating compositions, curable powder coating compositions and method for using the same |
US20050165133A1 (en) * | 2004-01-28 | 2005-07-28 | Xerox Corporation | Emulsion aggregation process for forming powder coating compositions, powder coating compositions and method for using the same |
US7279261B2 (en) | 2005-01-13 | 2007-10-09 | Xerox Corporation | Emulsion aggregation toner compositions |
US20060154167A1 (en) * | 2005-01-13 | 2006-07-13 | Xerox Corporation | Emulsion aggregation toner compositions |
US20070059630A1 (en) * | 2005-09-09 | 2007-03-15 | Xerox Corporation | Emulsion polymerization process |
US7713674B2 (en) | 2005-09-09 | 2010-05-11 | Xerox Corporation | Emulsion polymerization process |
US20080299478A1 (en) * | 2007-05-31 | 2008-12-04 | Xerox Corporation | Toner compositions |
US20080299479A1 (en) * | 2007-05-31 | 2008-12-04 | Xerox Corporation | Toner compositions |
US8455171B2 (en) | 2007-05-31 | 2013-06-04 | Xerox Corporation | Toner compositions |
US20090061342A1 (en) * | 2007-09-05 | 2009-03-05 | Xerox Corporation | Toner compositions |
US20090081576A1 (en) * | 2007-09-25 | 2009-03-26 | Xerox Corporation | Toner compositions |
US20090263740A1 (en) * | 2008-04-21 | 2009-10-22 | Xerox Corporation | Toner compositions |
US8092973B2 (en) | 2008-04-21 | 2012-01-10 | Xerox Corporation | Toner compositions |
US20100086701A1 (en) * | 2008-10-06 | 2010-04-08 | Xerox Corporation | Radiation curable ink containing fluorescent nanoparticles |
US8147714B2 (en) | 2008-10-06 | 2012-04-03 | Xerox Corporation | Fluorescent organic nanoparticles and a process for producing fluorescent organic nanoparticles |
US8222313B2 (en) | 2008-10-06 | 2012-07-17 | Xerox Corporation | Radiation curable ink containing fluorescent nanoparticles |
US8236198B2 (en) | 2008-10-06 | 2012-08-07 | Xerox Corporation | Fluorescent nanoscale particles |
EP2172812A1 (en) | 2008-10-06 | 2010-04-07 | Xerox Corporation | Toner containing fluorescent nanoparticles |
US8541154B2 (en) | 2008-10-06 | 2013-09-24 | Xerox Corporation | Toner containing fluorescent nanoparticles |
US8586141B2 (en) | 2008-10-06 | 2013-11-19 | Xerox Corporation | Fluorescent solid ink made with fluorescent nanoparticles |
US10294355B2 (en) | 2014-10-13 | 2019-05-21 | Avery Dennison Corporation | Vinyl acetate-ethylene/acrylic polymer emulsions and products and methods relating thereto |
EP3133115A1 (en) | 2015-08-14 | 2017-02-22 | King Abdulaziz City for Science and Technology | Polymer-encapsulated carbon black: process for its preparation and use thereof |
Also Published As
Publication number | Publication date |
---|---|
EP1088833A1 (en) | 2001-04-04 |
JP2001131214A (en) | 2001-05-15 |
DE60010192D1 (en) | 2004-06-03 |
DE60010192T2 (en) | 2004-08-26 |
US20020049275A1 (en) | 2002-04-25 |
EP1088833B1 (en) | 2004-04-28 |
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